Dear Prudie,
I have been seeing a really sweet guy for three months. He is intelligent, fun, considerate, and generous. My issue is that he is a virgin and doesn't seem very interested in changing that. We are both in our early 30s. I am recently divorced—my husband was a compulsive cheat—and have a 2-year-old son. I have discussed sex with “James” and he said that he originally wanted to wait until marriage for religious reasons, but now doesn't feel that is necessary, he just wants it to be with the right person. We were making out the other night and I whispered to him how much I wanted him. He said he wanted me, too, but he sounded awkward and unconvincing. He always tells me that we can't do anything because he doesn't have condoms, but he hasn't made any attempts to purchase some. I can tell he is aroused when we kiss, but I’m worried that he just isn't very interested in sex. That would be tough for me to handle long term. Is it wrong that I expect our relationship to be further along after three months? My friends say I need a man with more heat and passion but I am hesitant to pass up an otherwise great guy.

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—Thirty-Year-Old Virgin

Dear Virgin,
“I don’t have a condom” is “The dog ate my homework” of the lifetime virgin. You say you’re worried he’s not interested in sex. Since he’s never had it, despite your giving him the opportunity, you may be onto something. Of course, it’s possible he is interested in sex but, having gotten to this point in life without knowing what to do, he may be terrified about disappointing a sophisticated woman like you. It could be that he has some kind of sexual hang-up, or feels self-conscious about his body for some reason. But here he is, with a knowledgeable partner eager to get him over the hump, and he keeps balking. You have just been deeply hurt by the man you thought you would spend your life with, and I understand there is not an abundance of lovely, eligible men. But having a partner you’re certain will never cheat on you because he’s apparently incapable of doing the deed is not the answer. You also must know that even if you do get him in bed, it’s likely to be a frustrating experience. See the hilarious consummation scene at the end of The 40-Year-Old Virgin. I believe in the value of going slow, but three months is long enough to see if a relationship is worth investing more time; one way to find out is to explore your sexual compatibility. If you’re willing to lead the guy by the hand, then have a discussion with him explaining you think it’s time, and you will purchase the condoms. If you two still can’t get into bed, that’s evidence enough your relationship won’t survive outside it.

—Prudie

Dear Prudence: Failure to Communicate

Dear Prudence,
My wife and I have been married for 18 months and have a baby girl. We have a strong marriage. When we were engaged, I noticed that my future wife was spending lots of money on fancy name brand items. She does not come from a wealthy family and it was concerning to me. About two weeks before our wedding I went shopping with her and her sister and they confessed and told me that they wear most of the items once and return them. I was a bit floored as I come from a very honest hard-working family, and we would never stoop so low. What she does makes me sick, and I have confronted her many times about this, but I can't get through. My respect for her and her family has taken a hit. I don’t want our children thinking this is acceptable behavior. I want them to know that through hard work they can obtain the items they want, but also that it isn't necessary to show off your brand names. This has become the underlying issue in most of our arguments.

—Keep It

Dear Keep It,
Your wife has unlocked the secret of how to be a woman who never wears the same thing twice—and never pays for it, either. What your wife does is bad for retailers’ bottom line, but it’s better for yours that she’s a compulsive returner and not just a compulsive shopper. I share your distaste for this practice. This recent Wall Street Journalarticle shows that while Nordstrom’s will take back just about anything, the return is then subtracted from the commission of the original sales person. And this follows up on another Journalstory on how sporting goods retailer REI had to limit its return policy from forever to one year, because too many customers were returning worn items bought decades ago. I agree your wife is being somewhat dishonest—although let’s give her credit for wearing the stuff only once—and that she should build a real instead of virtual wardrobe, one she can afford. But you’re not going to win this argument. I bet the whole process of selecting items beyond her budget, showing up dressed to kill, then getting her money back gives her a kind of high. You’ve said your piece about her rag trade, and this simply is not worth collapsing your marriage over. Since the retailers won’t even back you up, you need to back off. Let’s just hope stores start balking when your wife tries to return spittle-covered onesies your daughter has outgrown.

Dear Prudence,
I'm wondering if I should quit my job. I’m a 27-year-old woman who works as a program manager at a nonprofit that promotes access to healthy food. When I was hired at the beginning of the year, it was as an assistant manager, and I was thrilled. This was my first full time job after years of juggling two to three part-time jobs, and I looked forward to gaining experience and new skills. A few months later the program manager was let go and I was asked to take over. I expressed trepidation, but was assured by my supervisors that they had confidence in me. I constantly feel like I'm failing, that I’m missing things and making mistakes and just muddling through. It kills me to think that my incompetence could be hindering our fantastic mission. In addition, the stress is really getting to me. My supervisor seems be to be satisfied with my performance, but I want to go back to being an assistant. Am I crazy to ask for a demotion? Should I just try to keep it together and hope no one notices that I'm panicking?

—Over My Head

Dear Over,
As scary and vertiginous as this is, you should continue to step up and lean in (which I admit sounds like dizzying advice). It doesn’t appear that you were just a warm body making a lower salary that prompted management to tap you for this job. Your bosses saw something in your work they liked and you apparently continue to satisfy them, even if not yourself. Like many millennials, you have had a hard time getting a toehold in a career. So you should think long and hard before trying to step down a rung. It’s understandable you feel overwhelmed and not ready for the job. But you have it, so take action to make yourself more competent. Find out if there are evening classes in nonprofit management at nearby colleges. If not, search out reputable online programs. Get helpful bedtime reading. Here are a couple of books you can start with: Managing the Nonprofit OrganizationandThe Charismatic Organization. Ask your supervisor to have a weekly meeting in which you discuss goals and how to implement them. Also make sure you’re eating right, exercising, and getting enough sleep. Stress multiplies when you’re physically run down. Recognize that what you are feeling is not uncommon. If everyone who worried they weren’t up to the task left their job, the unemployment rate would be astronomical.

—Prudie

Dear Prudence,My son recently divorced a woman he had been briefly married to, who has returned home to the European country where he met her. She couldn’t find a job in the States and came to loathe all things American, including my son. She sent me an email full of criticisms of him and all the “bad things” he had done while they were married. I figured this was just an example of her character, but one thing has stayed with me. She said that my son fathered a child by his previous fiancée. My son had told me previously that this woman had had a child and I asked him directly if he was the father. He said he wasn’t. The divorce has been very hard on my son, and I haven’t mentioned the ex’s email, but I keep wondering if I have a grandchild. Both my children are in their 30s and I don’t see any other grandchildren in the foreseeable future. It would break my heart if I have a grandchild I will never meet. Do I have a right to know? And how should I approach this with my son?

—Want to Be a Grandma

Dear Want,
This real but also figmentary child is not going to fulfill your understandable wishes to be a grandmother. You asked your son point blank if this child was his, and he denied paternity. But let’s say he does assume or know that he is the father of his ex-fiancée’s child. Then it’s most odd that this would be a secret, that he wouldn’t be supporting this child, and that the baby would have no place in his life. If that’s the case, the two adults involved have likely decided on this course of action, and your aching heart is not going to change that. However, it’s fair enough, since you’ve already talked about this issue with your son, to say that you got a nasty email from his ex making this assertion. Explain you dismissed most of what she wrote, but that you’re troubled thinking there is a child of his out there that none of you knows. If he shrugs it off, accept that it’s far from too late for your children to eventually produce another generation.

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More Dear Prudence Chat Transcripts

“Occupy the Dollhouse: In a live chat, Prudie advises a mother whose niece flaunts her expensive toys in front of her cousins.”
“Toilet Paper: In a live chat, Prudie advises a man whose co-worker always takes the office newspaper to the bathroom.”
“Me or the Dog: In a live chat, Prudie advises a woman whose boyfriend wants her to give away her cocker spaniel.”
“Snip and Tell: In a live chat, Prudie advises a woman who’s been trying to get pregnant—only to find out her husband had a secret vasectomy.”